Process of preparing condensation products of the benzanthrone series and new products obtainable thereby



' chloric acid the crude acid is Patented Feb. 20, 1934 UNITED STATES PATENT on 1,947,943 ICE,

PROCESS SERIES AND ABLE THEREBY OF PREPARING PRODUCTS OF THE NEW PRODUCTS OBTAIN- CONDENSATION BEN ZAN THBONEI Georg Kraenzlein, Frankfort on the- Main Hochst, and Martin Ccrell, Frankfort-on-the- Main, Works, of Delaware No Drawing. Application. January 27,

423,893, and in Germany February Serial No. 7, 1929 8 Claims.

The present invention relates to a new process of preparing condensation products of the benzanthrone series and to new products obtainable thereby.

We have found that condensation products of the benzanthrone ing with aluminium chloride particularly sodium aluminium chloride a compound of the general formula:

wherein X represents a hydroxylalkoxylor amino group. The process is preferably carried out at an elevated temperature as for instance between C.-200 C. We prefer to use a temperature of about C.160 C. The new products obtainable according to our new process are The following examples illustrate the invention, but they are not intended to limit it thereto, the parts being by weight:

(1). 200 parts of benzoic acid ester of 2.3-hytated by means of hydrochloric acid. When recrystallized from glacial acetic acid the acid forms Germany, assignors to General Aniline Inc., New York,

N. Y., a corporation a solution of dilute sodium carbonate, filtered and the l-hydroxyb'enzanthrone-B-carboxylic acid is precipitated. It is identical with the acid described in Example 1. r

(3). 100 parts of Bz-m-chloro-benzoic acid ester of 2.3-hydroxynaphthoic acid ethylester of the formula:

oo OO Ol C. are molten together with 1,100 parts of sodium aluminium chloride for about 10 hours at C..-- C. The. molten mass is worked up as described in Example 1. The 4-hydroxy-6-chlorobenzanthrone-3-carboxylic acid obtained dissolves in concentrated sulfuric acid to an orange solution having a brown fluorescence and melting at 250 C.252 C.

We claim:

1. The process which comprises heating with aluminium chloride a compound of the following general formula:

and melting at 112 wherein X represents a hydroXyl-, alkoxylor amino group and Y represents an aryl of the benzene series.

2. The process which comprises heating with aluminium chloride at a temperature of about 100 C. to 200 C. a compound of the following general formula:

The 4-hydroxybenzanthrone-3-carboxylic acid a hydroxyl-, alkoxylor aryl of the wherein X represents amino group and Y represents an benzene series.

3. The process which comprises heating with aluminium chloride at a temperature of about 140 C. to 160 C. a compound of the following general formula:

wherein X represents a hydroxyl-, alkoxylor iii amino group and Y benzene series. I

4. The process which comprises melting with sodim aluminium chloride at a temperature of about C.to 200 C. a compound of the following general formula:

represents an aryl of the wherein X represents a hydroxyl-, alkoxylor amino group and Y represents an aryl of the benzene series.

5. The process which comprises melting with sodium aluminium chloride at a temperature of about 150 C. to 160 C. the benzoic acid ester of 2.3-naphthoic acid of the following formula:

COOH

6. The compound of the following formula:

-COOH melting at 285 C. and crystallizing from glacial acetic acid in yellow needles.

'7. The compound of the following formula:

dissolving in concentrated sulfuric acid to an orange solution having a melting at 250 C.-252 C 8. The compounds of COOH brown fluorescence and the following formula:

wherein the benzene nucleus B may contain a halogen atom as a substituent, crystallizing from glacial acetic acid and showing a fluorescence in a concentrated sulfuric acid solution.

GEORG KRAENZLEIN. MARTIN CORELL. 

